Hydrochloric Acid → 4-Hydroxy-2,3-dihydro-1H-indene-5-carbaldehyde

HRID 1099368Notes

Reaction equation

[Cl-].[Mg+2].[Cl-].[CH2:4]=[O:5].C(N(CC)CC)C.[CH2:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:22])[C:16]=2[CH2:15][CH2:14]1.Cl>O1CCCC1>[OH:22][C:17]1[C:18]([CH:4]=[O:5])=[CH:19][CH:20]=[C:21]2[C:16]=1[CH2:15][CH2:14][CH2:13]2

Participants

Conditions

Temperature: 72.5 °C

Procedure

To a stirred suspension Magnesium chloride (71.0 gm, 0.745 mole) and Para-formaldehyde (33.6 gm, 1.12 mole) in Tetrahydrofuran (200 ml), Triethylamine (104 ml, 0.745 mole) was added at room temperature and stirred for 30 minutes. To the reaction mixture; the solution of Indan-4-ol (50 gm, 0.373) in Tetrahydrofuran (100 ml) was added at room temperature and heated to 70-75° C. for 6 hours. To the reaction mixture, 2N Hydrochloric acid (600 ml) was added and extracted with Ethylacetate (2×500 ml). The Ethylacetate layer was washed with water (300 ml), dried over Sodium sulphate and further it was distilled under vacuum to give viscous oil (52.0 gm) which becomes solid upon keeping.

Workup

extractionextracted with Ethylacetate (2×500 ml)
washThe Ethylacetate layer was washed with water (300 ml)
dry with materialdried over Sodium sulphate and further it
distillationwas distilled under vacuum

Sources & evidence

ORD record: ord-d93df2d7064e4f0594359a8cbb79fd26
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143424B2

Reaction notes

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